ADDITION OF LITHIATED METHOXYALLENE TO AZIRIDINES - A NOVEL ACCESS TO ENANTIOPURE PIPERIDINE AND beta-AMINO ACID DERIVATIVES

作者：Prisyazhnyuk Vladimir; Jachan Matthias; Bruedgam Irene; Zimmer Reinhold; Reissig Hans Ulrich^*

来源：Collection of Czechoslovak Chemical Communications, 2009, 74(7-8): 1069-1080.

DOI：10.1135/cccc2009012

• Allenes
• Aziridines
• Alkynes
• Piperidones
• Benzomorphan
• beta-Amino ester

Addition of lithiated methoxyallene to aziridine derivatives provided the expected primary addition products. The less substituted carbon of the aziridine ring was attacked selectively. The primary adducts could be converted to enantiopure piperidine derivatives or beta-amino acid derivatives. The unexpected reactions lead to a tricyclic sulfonamide and to alkynyl-substituted aminoethers. The efficient two-step conversion of a piperidone derivative to a benzomorphan demonstrates the potential of this approach to biologically active compounds.

• 出版日期2009